JP2014501269A5 - - Google Patents
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- Publication number
- JP2014501269A5 JP2014501269A5 JP2013546715A JP2013546715A JP2014501269A5 JP 2014501269 A5 JP2014501269 A5 JP 2014501269A5 JP 2013546715 A JP2013546715 A JP 2013546715A JP 2013546715 A JP2013546715 A JP 2013546715A JP 2014501269 A5 JP2014501269 A5 JP 2014501269A5
- Authority
- JP
- Japan
- Prior art keywords
- urea
- quinolin
- pyridin
- pyran
- heterocyclic compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000002391 heterocyclic compounds Chemical class 0.000 claims 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- -1 C 1 -C 6 -alkoxy Chemical group 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 9
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
- 239000004202 carbamide Substances 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 claims 3
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 3
- 230000002285 radioactive effect Effects 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- VQPBIJGXSXEOCU-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC1=CC=CC(C(F)(F)F)=N1 VQPBIJGXSXEOCU-UHFFFAOYSA-N 0.000 claims 2
- GWCWCWXMAZCRIV-UHFFFAOYSA-N 1-[6-(3,4-dihydro-2h-pyran-5-yl)pyridin-2-yl]-3-(8-fluoroquinolin-4-yl)urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1=COCCC1 GWCWCWXMAZCRIV-UHFFFAOYSA-N 0.000 claims 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 150000001975 deuterium Chemical group 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 2
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- HUIGDQIGGTVHLC-UHFFFAOYSA-N 1-(1,5-naphthyridin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC=CN=C2C=1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 HUIGDQIGGTVHLC-UHFFFAOYSA-N 0.000 claims 1
- NUVBOUNAXOEMGL-UHFFFAOYSA-N 1-(5,8-difluoroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=C(F)C2=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 NUVBOUNAXOEMGL-UHFFFAOYSA-N 0.000 claims 1
- KJDGNNMYOYVDES-UHFFFAOYSA-N 1-(6,8-dichloroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(Cl)=CC(Cl)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 KJDGNNMYOYVDES-UHFFFAOYSA-N 0.000 claims 1
- YVCQZVBSYKUTNJ-UHFFFAOYSA-N 1-(6,8-difluoroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(F)=CC(F)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 YVCQZVBSYKUTNJ-UHFFFAOYSA-N 0.000 claims 1
- AUBIMDGQGZMWTM-UHFFFAOYSA-N 1-(6,8-difluoroquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C12=CC(F)=CC(F)=C2N=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=N1 AUBIMDGQGZMWTM-UHFFFAOYSA-N 0.000 claims 1
- PYOMPXLAYCWFPK-UHFFFAOYSA-N 1-(6-bromoquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(Br)=CC=C3N=CC=2)=N1 PYOMPXLAYCWFPK-UHFFFAOYSA-N 0.000 claims 1
- HXBDFOQTPGIDNA-UHFFFAOYSA-N 1-(6-cyclopropylpyrazin-2-yl)-3-(6-piperidin-4-ylquinolin-4-yl)urea Chemical compound C=1C=NC2=CC=C(C3CCNCC3)C=C2C=1NC(=O)NC(N=1)=CN=CC=1C1CC1 HXBDFOQTPGIDNA-UHFFFAOYSA-N 0.000 claims 1
- OKGRTJOEILSKSR-UHFFFAOYSA-N 1-(6-cyclopropylpyrazin-2-yl)-3-[6-(1-methylpiperidin-4-yl)quinolin-4-yl]urea Chemical compound C1CN(C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=NC=3)C3CC3)C2=C1 OKGRTJOEILSKSR-UHFFFAOYSA-N 0.000 claims 1
- JDLZNEXCJIZHBW-UHFFFAOYSA-N 1-(6-piperidin-4-ylquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C2CCNCC2)=N1 JDLZNEXCJIZHBW-UHFFFAOYSA-N 0.000 claims 1
- RISTYTNTGUCKRV-UHFFFAOYSA-N 1-(6-piperidin-4-ylquinolin-4-yl)-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC=C(C3CCNCC3)C=C2C=1NC(=O)NC1=CN=CC=N1 RISTYTNTGUCKRV-UHFFFAOYSA-N 0.000 claims 1
- YYJKBJITPDPGDD-UHFFFAOYSA-N 1-(7-bromoquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=C(Br)C=C3N=CC=2)=N1 YYJKBJITPDPGDD-UHFFFAOYSA-N 0.000 claims 1
- VDEZAETUSYBUSQ-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-[6-(oxan-3-yl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC(N=1)=CC=CC=1C1CCCOC1 VDEZAETUSYBUSQ-UHFFFAOYSA-N 0.000 claims 1
- OVIADVAXXQTSSR-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 OVIADVAXXQTSSR-UHFFFAOYSA-N 0.000 claims 1
- RLJBDBYYVSSBOT-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC1=CN=CC=N1 RLJBDBYYVSSBOT-UHFFFAOYSA-N 0.000 claims 1
- OHHJJQZGSOYSCF-UHFFFAOYSA-N 1-(8-chloro-6-methylquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(C)=CC(Cl)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 OHHJJQZGSOYSCF-UHFFFAOYSA-N 0.000 claims 1
- CINSMAXRSWIPNW-UHFFFAOYSA-N 1-(8-chloroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(Cl)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 CINSMAXRSWIPNW-UHFFFAOYSA-N 0.000 claims 1
- JQJSZQPPZOVZSA-UHFFFAOYSA-N 1-(8-cyanoquinolin-4-yl)-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=C(C#N)C=CC=C2C=1NC(=O)NC1=CN=CC=N1 JQJSZQPPZOVZSA-UHFFFAOYSA-N 0.000 claims 1
- WMDXIIORGIWVQV-UHFFFAOYSA-N 1-(8-fluoro-6-methoxyquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(OC)=CC(F)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 WMDXIIORGIWVQV-UHFFFAOYSA-N 0.000 claims 1
- MIBNRIDIGPQNKR-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-(6-piperidin-4-ylpyridin-2-yl)urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCNCC1 MIBNRIDIGPQNKR-UHFFFAOYSA-N 0.000 claims 1
- WSNGAJHTEQWBIM-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[5-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=C1)=CC=C1C1CCOCC1 WSNGAJHTEQWBIM-UHFFFAOYSA-N 0.000 claims 1
- CJMDXGWKXLQJEY-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[6-(1-propan-2-ylpiperidin-4-yl)pyridin-2-yl]urea Chemical compound C1CN(C(C)C)CCC1C1=CC=CC(NC(=O)NC=2C3=CC=CC(F)=C3N=CC=2)=N1 CJMDXGWKXLQJEY-UHFFFAOYSA-N 0.000 claims 1
- XGYJOSADRJVTBY-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[6-(oxan-3-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCCOC1 XGYJOSADRJVTBY-UHFFFAOYSA-N 0.000 claims 1
- LMBZXVCPBNGXGR-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 LMBZXVCPBNGXGR-UHFFFAOYSA-N 0.000 claims 1
- RMWWSSJQQBSPNH-UHFFFAOYSA-N 1-[6-(1,2,3,6-tetrahydropyridin-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C=2CCNCC=2)=N1 RMWWSSJQQBSPNH-UHFFFAOYSA-N 0.000 claims 1
- YCEGRQBTGLDCDA-UHFFFAOYSA-N 1-[6-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1N(C)CCC(C=2C=C3C(NC(=O)NC=4N=C(C=CC=4)C(F)(F)F)=CC=NC3=CC=2)=C1 YCEGRQBTGLDCDA-UHFFFAOYSA-N 0.000 claims 1
- VHYMKHPSLVPMPC-UHFFFAOYSA-N 1-[6-(1-methylpiperidin-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1CN(C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 VHYMKHPSLVPMPC-UHFFFAOYSA-N 0.000 claims 1
- FQVMTXVNXUTWIN-UHFFFAOYSA-N 1-[6-(1-methylpiperidin-4-yl)quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C1CN(C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=CC=NC=3)C2=C1 FQVMTXVNXUTWIN-UHFFFAOYSA-N 0.000 claims 1
- QFLPJUZAYALTDE-UHFFFAOYSA-N 1-[6-(2,5-dihydro-1h-pyrrol-3-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C=2CNCC=2)=N1 QFLPJUZAYALTDE-UHFFFAOYSA-N 0.000 claims 1
- HDQBKWBMALHQDI-UHFFFAOYSA-N 1-[6-(3,4-dihydro-2h-pyran-5-yl)pyridin-2-yl]-3-(7-methoxyquinolin-4-yl)urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC(N=1)=CC=CC=1C1=COCCC1 HDQBKWBMALHQDI-UHFFFAOYSA-N 0.000 claims 1
- DSWADQAUCOSMPB-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)pyridin-2-yl]-3-(1,5-naphthyridin-4-yl)urea Chemical compound C=1C=NC2=CC=CN=C2C=1NC(=O)NC(N=1)=CC=CC=1C1=CCOCC1 DSWADQAUCOSMPB-UHFFFAOYSA-N 0.000 claims 1
- BYKSEVADXIBXTH-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)pyridin-2-yl]-3-(8-fluoroquinolin-4-yl)urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1=CCOCC1 BYKSEVADXIBXTH-UHFFFAOYSA-N 0.000 claims 1
- XGMXDYRMLPAZKF-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C=2CCOCC=2)=N1 XGMXDYRMLPAZKF-UHFFFAOYSA-N 0.000 claims 1
- TVXURCBJJQDUAY-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC=C(C=3CCOCC=3)C=C2C=1NC(=O)NC1=CN=CC=N1 TVXURCBJJQDUAY-UHFFFAOYSA-N 0.000 claims 1
- VSAVKIVEYJZKSW-UHFFFAOYSA-N 1-[6-(oxan-3-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C2COCCC2)=N1 VSAVKIVEYJZKSW-UHFFFAOYSA-N 0.000 claims 1
- VXQWZNGQNKCLKD-UHFFFAOYSA-N 1-[6-(oxan-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C2CCOCC2)=N1 VXQWZNGQNKCLKD-UHFFFAOYSA-N 0.000 claims 1
- XFRYMFRHCLWJQY-UHFFFAOYSA-N 1-[6-(trifluoromethyl)pyridin-2-yl]-3-[7-(trifluoromethyl)quinolin-4-yl]urea Chemical compound C=1C=NC2=CC(C(F)(F)F)=CC=C2C=1NC(=O)NC1=CC=CC(C(F)(F)F)=N1 XFRYMFRHCLWJQY-UHFFFAOYSA-N 0.000 claims 1
- FBWWNLBZZFVRQY-UHFFFAOYSA-N 1-[6-(trifluoromethyl)pyridin-2-yl]-3-[8-(trifluoromethyl)quinolin-4-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=N1 FBWWNLBZZFVRQY-UHFFFAOYSA-N 0.000 claims 1
- VBISSAFCYVKVAC-UHFFFAOYSA-N 1-[6-[1-(2,2-difluoroethyl)piperidin-4-yl]pyridin-2-yl]-3-(8-fluoroquinolin-4-yl)urea Chemical compound C1CN(CC(F)F)CCC1C1=CC=CC(NC(=O)NC=2C3=CC=CC(F)=C3N=CC=2)=N1 VBISSAFCYVKVAC-UHFFFAOYSA-N 0.000 claims 1
- DCHDMOPFMYEBSB-UHFFFAOYSA-N 1-[6-[1-(2,2-difluoroethyl)piperidin-4-yl]quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1CN(CC(F)F)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 DCHDMOPFMYEBSB-UHFFFAOYSA-N 0.000 claims 1
- HEFHJWMRPPVCTR-UHFFFAOYSA-N 1-[6-[1-(2-fluoroethyl)piperidin-4-yl]quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1CN(CCF)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 HEFHJWMRPPVCTR-UHFFFAOYSA-N 0.000 claims 1
- XFPMVDJORHOMMD-UHFFFAOYSA-N 1-[6-[1-(2-fluoroethyl)piperidin-4-yl]quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C1CN(CCF)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=CC=NC=3)C2=C1 XFPMVDJORHOMMD-UHFFFAOYSA-N 0.000 claims 1
- NQGMRQWIVQLMHW-UHFFFAOYSA-N 1-[7-(3,4-dihydro-2h-pyran-5-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=C(C=C3N=CC=2)C=2CCCOC=2)=N1 NQGMRQWIVQLMHW-UHFFFAOYSA-N 0.000 claims 1
- NKOFCVPOYFPQHF-UHFFFAOYSA-N 1-[7-(3,6-dihydro-2h-pyran-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=C(C=C3N=CC=2)C=2CCOCC=2)=N1 NKOFCVPOYFPQHF-UHFFFAOYSA-N 0.000 claims 1
- MUANCMSIGNOISO-UHFFFAOYSA-N 1-[7-(3,6-dihydro-2h-pyran-4-yl)quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC(C=3CCOCC=3)=CC=C2C=1NC(=O)NC1=CN=CC=N1 MUANCMSIGNOISO-UHFFFAOYSA-N 0.000 claims 1
- KWVPRRBJZGHPPP-UHFFFAOYSA-N 1-[7-(oxan-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=C(C=C3N=CC=2)C2CCOCC2)=N1 KWVPRRBJZGHPPP-UHFFFAOYSA-N 0.000 claims 1
- BSBUFEFSAHPKBI-UHFFFAOYSA-N 1-[7-(oxan-4-yl)quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC(C3CCOCC3)=CC=C2C=1NC(=O)NC1=CN=CC=N1 BSBUFEFSAHPKBI-UHFFFAOYSA-N 0.000 claims 1
- OFHYJGIWOBCELM-UHFFFAOYSA-N 1-pyrazin-2-yl-3-(6-pyrrolidin-3-ylquinolin-4-yl)urea Chemical compound C=1C=NC2=CC=C(C3CNCC3)C=C2C=1NC(=O)NC1=CN=CC=N1 OFHYJGIWOBCELM-UHFFFAOYSA-N 0.000 claims 1
- COCKHBFAABWZBN-UHFFFAOYSA-N 1-pyrazin-2-yl-3-[6-(1,2,3,6-tetrahydropyridin-4-yl)quinolin-4-yl]urea Chemical compound C=1C=NC2=CC=C(C=3CCNCC=3)C=C2C=1NC(=O)NC1=CN=CC=N1 COCKHBFAABWZBN-UHFFFAOYSA-N 0.000 claims 1
- IEDGRSYITLMBAN-UHFFFAOYSA-N 1-quinolin-4-yl-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=CC=C3N=CC=2)=N1 IEDGRSYITLMBAN-UHFFFAOYSA-N 0.000 claims 1
- 125000001627 3 membered heterocyclic group Chemical group 0.000 claims 1
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
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- GZNADDRJCSQZJF-UHFFFAOYSA-N tert-butyl 3-[4-(pyrazin-2-ylcarbamoylamino)quinolin-6-yl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=CC=NC=3)C2=C1 GZNADDRJCSQZJF-UHFFFAOYSA-N 0.000 claims 1
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- HJULFMJNYVIQIN-UHFFFAOYSA-N tert-butyl 4-[4-(pyrazin-2-ylcarbamoylamino)quinolin-6-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=C3C(NC(=O)NC=4N=CC=NC=4)=CC=NC3=CC=2)=C1 HJULFMJNYVIQIN-UHFFFAOYSA-N 0.000 claims 1
- GIACGSWLXZCBGT-UHFFFAOYSA-N tert-butyl 4-[4-[(6-cyclopropylpyrazin-2-yl)carbamoylamino]quinolin-6-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=NC=3)C3CC3)C2=C1 GIACGSWLXZCBGT-UHFFFAOYSA-N 0.000 claims 1
- YEJAFXVKMRTNJM-UHFFFAOYSA-N tert-butyl 4-[4-[[6-(trifluoromethyl)pyridin-2-yl]carbamoylamino]quinolin-6-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=C3C(NC(=O)NC=4N=C(C=CC=4)C(F)(F)F)=CC=NC3=CC=2)=C1 YEJAFXVKMRTNJM-UHFFFAOYSA-N 0.000 claims 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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| US61/521,868 | 2011-08-10 | ||
| PCT/EP2011/074272 WO2012089828A2 (en) | 2010-12-30 | 2011-12-30 | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
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| JP2017011851A Pending JP2017122089A (ja) | 2010-12-30 | 2017-01-26 | 複素環化合物およびグリコーゲンシンターゼキナーゼ−３阻害薬としてのそれの使用 |
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| US9090592B2 (en) * | 2010-12-30 | 2015-07-28 | AbbVie Deutschland GmbH & Co. KG | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
| JP6534098B2 (ja) * | 2014-09-12 | 2019-06-26 | 国立大学法人 鹿児島大学 | 成人ｔ細胞白血病治療薬 |
| US11248007B2 (en) * | 2017-03-08 | 2022-02-15 | Cornell University | Inhibitors of MALT1 and uses thereof |
| RU2739489C2 (ru) * | 2018-03-06 | 2020-12-24 | Закрытое Акционерное Общество "Биокад" | Новые гетероциклические соединения как ингибиторы CDK8/19 |
| CA3115493A1 (en) * | 2018-10-17 | 2020-04-23 | Duke University | Quinone reductase 2 inhibitors for use as neuroprotective agents |
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-
2011
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- 2011-12-30 CN CN201180068418.0A patent/CN103476766B/zh not_active Expired - Fee Related
- 2011-12-30 JP JP2013546715A patent/JP6144201B2/ja not_active Expired - Fee Related
- 2011-12-30 BR BR112013016928-1A patent/BR112013016928A2/pt not_active IP Right Cessation
- 2011-12-30 EP EP17206645.8A patent/EP3351543A1/en not_active Withdrawn
- 2011-12-30 MX MX2013007702A patent/MX336346B/es unknown
- 2011-12-30 CA CA2821863A patent/CA2821863A1/en not_active Abandoned
- 2011-12-30 SG SG10201406098UA patent/SG10201406098UA/en unknown
- 2011-12-30 NZ NZ611314A patent/NZ611314A/en not_active IP Right Cessation
- 2011-12-30 RU RU2013135477A patent/RU2623427C2/ru not_active IP Right Cessation
- 2011-12-30 AU AU2011351375A patent/AU2011351375B2/en not_active Ceased
- 2011-12-30 KR KR1020137020021A patent/KR101860297B1/ko not_active Expired - Fee Related
- 2011-12-30 WO PCT/EP2011/074272 patent/WO2012089828A2/en active Application Filing
- 2011-12-30 EP EP11811357.0A patent/EP2658854B1/en not_active Not-in-force
- 2011-12-30 SG SG2013050703A patent/SG191789A1/en unknown
-
2013
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- 2013-06-25 ZA ZA2013/04756A patent/ZA201304756B/en unknown
-
2015
- 2015-06-15 US US14/740,048 patent/US9540370B2/en not_active Expired - Fee Related
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2017
- 2017-01-26 JP JP2017011851A patent/JP2017122089A/ja active Pending
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